“Are you riding across the country or something?” she asks, eyeing his sturdy royal blue bike and its unusual trappings: A New York license plate adorns its handlebars, and a hitched neon-yellow trailer follows close behind.

“Yeah,” Tanenhaus says with a nod and a grin.

“Seriously? … Well you deserve an apple.”

Moments later, Tanenhaus has a Razor Russett—a spicier, browner version of a Golden Delicious—in hand, and is wished a “Happy Journey” by his new acquaintance.

Such encounters are uplifting and astoundingly regular for the 35-year-old cyclist, who is undertaking an unusual adventure. On August 6, Tanenhaus quit his job in event planning, hopped astride a Citi Bike—the official vehicle of New York City’s bike share program—and began racking up miles from Manhattan to Los Angeles. “When I decided to go across country,” he says, “I knew which bike it had to be.”

A Citi Bike wouldn’t be most cyclist’s first choice of steed for a bikepacking adventure. Never mind that he’s already had to pay the maximum $1,200 in late fees (plus tax!) for exceeding the 45-minute use limit, or that Citi Bike has not endorsed his trip. “I only had one conversation with them directly,” he says. “They could not support me, but it wasn’t like they said, ‘If you do this, you’re going to wind up in jail.’”

Then there’s the fact that the bike is a 45-pound behemoth with just three gears. Tanenhaus has to walk it up most hills—and there’s an antilock system on the tires that makes changing a flat impossible (good thing they’re puncture resistant). Nevertheless, Tanenhaus developed a special affinity for the hardy two-wheeler during the 18 months he spent riding it from his downtown Brooklyn apartment to his corporate job in Times Square.

Those 30-minute commutes—spent dodging cars and pedestrians, chugging across bridges, and negotiating potholes—were the best part of his day. “I had to focus just on making it to my destination,” he says. “It crowded out any thoughts of past disappointments or uncertainties about the future.”

Recreating that “present-in-the-moment feeling,” Tanenhaus says, as well as jump-starting a writing career that had gone stale—his new blog is countribike.com—were big reasons for the trip. But mostly, he’s hoping to learn about himself.

Fed up with his job and frustrated by New York’s high cost of living, he’s curious about what else is out there. “I used to think that if you weren’t living in New York, then where were you living?” he says. “And now that I go into smaller cities and towns, I see that there is life here and cool things to do, and there’s a real balance. Now I’m thinking, ‘Maybe these people have it right.’”

The trip is testing his resourcefulness and stamina. Tanenhaus, who originally hoped to ride 60 miles a day, has pared that down to 40. He has completed a couple of NYC Century Bike Tours in the past, and says, “If I were ever in trouble, there was always a subway, somewhere.” Now his most prized possessions are a reflective vest and his portable WiFi hotspot.

So far, the native New Yorker has pedaled just over 1,000 miles through New Jersey, Maryland, Washington, D.C., Pennsylvania, West Virginia, Ohio, and Indiana (where he last checked in). Along the way, he’s had uniformly positive encounters with strangers. He camps or uses the website warmshower.org to find fellow cyclists who will put him up for the night. One memorable night, a couple offered him use of their lake house for the weekend. On another, a member of Bike Pittsburgh, that city’s bike advocacy group, flagged him down and took him out for a beer.

Tanenhaus isn’t sure he’ll make it to LA—there’s the Rocky Mountains to consider, for one thing—but he hopes to get far enough that he might inspire a few people to treat riding a bike not only as a recreational pursuit, but also as true form of transportation. “I’m trying to show that by going across the country on a shared bike, maybe you can go across your town on a bike,” he says. “And maybe it will bring you some happiness, just like it did for me.”

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